How do you recrystallize phthalimide?
Phthalimide may be recrystallized from water, but only about 4 g. of phthalimide will dissolve in a liter of boiling water. It may also be crystallized from alcohol, in which solvent it dissolves to the extent of five parts in a hundred at boiling temperature.
What is structure of phthalimide?
Is phthalimide a good Nucleophile?
The phthalimide anion is a good nucleophile. When treated with various halogen containing compounds, it is alkylated in a manner quite similar to that observed in the alkylation of ammonia and of amines even though phthalimide is by no means an amine.
Is phthalimide toxic?
Safety. Phthalimide has low acute toxicity with LD 50 (rat, oral) of greater than 5,000 mg/kg.
Is Gabriel phthalimide a sn2?
The Gabriel Synthesis Uses A “Protected” Amine (Phthalimide) In An SN2 Reaction That Does Not Undergo Over-Alkylation.
Why is Gabriel’s phthalimide synthesis not used to prepare aniline?
Aniline cannot be prepared by Gabriel synthesis. Aniline cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.
What is the meaning of phthalimide?
: a crystalline weakly acidic cyclic compound C6H4(CO)2NH made usually by action of ammonia on phthalic anhydride and used chiefly in the synthesis of amines and amino acids, anthranilic acid, and formerly of indigo.
Which diuretic is phthalimide derivatives?
A thalidomide analogue used in combination with dexamethasone to treat patients with multiple myeloma. Phosmet is a phthalimide-derived organophosphate.
Which is the best phthalimide for amine deprotection?
Phthalimide groups are well-suited to this purpose, but would be more widely employed if deprotection could be achieved without resorting to hydrazinolysis. Because of that shortcoming, other more esoteric blocking groups such as the OX 7, N,N-diallyl 8 and STABASE 9 derivatives have been recommended as alternatives.
How are phthalimides converted to primary amines in one flask?
Phthalimides are converted to primary amines in an efficient, two-stage, one-flask operation using NaBH 4 /2-propanol, then acetic acid. Phthalimides of α-amino acids are smoothly deprotected with no measurable loss of optical activity. J. O. Osby, M. G. Martin, B. Ganem, Tetrahedron Lett., 1984, 25, 2093-2096.
What is the formula for the compound phthalimide?
Phthalimide is the organic compound with the formula C 6H 4(CO) 2NH. It is the imide derivative of phthalic anhydride. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base.
How is NaBH4 used to reduce phthalimides?
In 1961, two papers described the NaBH 4 reduction of phthalimides to complex product mixtures in a highly solvent, concentration and workup-dependent process 11,12 One group detected variable (but always low) yields of phthalide in some reductions 11.